Stereochemistry of Decahydroisoquinolines and Related Compounds. III. Syntheses of cis-2-Methyl-decahydro-7-isoquinolinols.

Abstract

Hydrogenation of isoquinolines, 2-methyl-1, 2, 3, 4-tetrahydro-7-isoquinolinol (V), 7-isoquinolinol (VII), 2-methyl-7-methoxy-1, 2, 3, 4-tetrahydroisoquinoline (IV), was carried out in three different ways. It was clarified that 2-methyl-2, 3, 4, 4α, 5, 6, 8, 8α-octahydro-7(1H)-isoquinolone (IX) and a pair of corresponding 2-methyl-decahydro-7-isoquinolinols (VIa and VIb), thus obtained, possessed cis configuration at ring juncture. In addition, hydrolysis products of 7-methoxy-1, 2, 3, 4, 5, 8-hexahydroisoquinoline (X) were discussed.